Itinerary · Italy
Rome, Florence and Venice, three nights each, a day in the Tuscan hills, and every move between them arranged before you land.
This is the first Italy trip I build most often, and the one I’d book for anyone seeing all three cities for the first time.
Three nights in each city is the minimum I’d give it. Any fewer and the trip becomes check-ins and check-outs. The transfers are written in below exactly as I book them: a driver waiting at arrivals, porters at the stations, a water taxi to your hotel’s own dock. You never carry a bag. Work with me and you get Fora perks at the hotels, typically a space-available upgrade, daily breakfast and a hotel credit, plus someone who knows these hotels personally. Same rate as booking direct.
How I choose between a car, a boat, a helicopter and the train is all on Getting around Italy.
Fly into Rome, home from Venice. Nine nights, ten days.
Your driver is in the arrivals hall at Fiumicino with your name on a sign, and about 45 minutes later you’re at Hotel de Russie, between the Spanish Steps and Piazza del Popolo. Lunch in the courtyard, an hour in the spa, an early night.
The move: Mercedes from Fiumicino, bags handled from the carousel to your room.
One morning for the Vatican with a private guide, timed for the first entry of the day. One for the Colosseum and the Forum. Keep the afternoons loose: a long lunch, the Pantheon, the walk back through the center.
One evening, have dinner on the rooftop at La Minerva, facing the Pantheon. A driver is on call for both days, so the heat and the distances never decide your plans.
Check out after breakfast and you’re in Florence before lunch. This is one of the two legs where I book the train, because it’s twice as fast as the road. Afternoon in the Oltrarno, aperitivo by the river.
The move: driver to the station, met with your name on a sign, porters take your bags to your seat in the top class on the fast train. About 1 hour 30. Met on the platform at Santa Maria Novella and driven to the hotel. Prefer the road? A private car takes about three hours, or I can arrange a helicopter.
The Uffizi and the Duomo with a private guide in the morning, before the city fills up. A long lunch, then the afternoon at the Four Seasons, whose private park is the quietest place in Florence.
Out into Chianti or the Val d’Orcia for wineries and hill towns, with lunch at one of the estates I know, Borgo San Felice or Il Borro. Back in Florence for dinner.
The move: a private driver who knows the back roads, so nobody has to choose between the tasting and the drive home. If you want the drive itself, I’ll have a supercar waiting at the hotel.
A little over two hours on the fast train, then the best arrival in Italy: out of Santa Lucia station and straight onto the water. Your hotel boat or water taxi is waiting at the station’s own dock.
The move: the same meet-and-greet and porters at both stations, then a private water taxi to Airelles Palladio on Giudecca. You never touch your luggage between Florence and your suite.
One day for San Marco with a private guide, early, before the day-trippers. One on the water: a private boat out to Murano, Burano and Torcello, with lunch on the way. Three nights is the sweet spot for Venice; at Airelles Palladio I could easily do four.
The move: the hotel boat makes the crossing to St. Mark’s in about five minutes, and I book the private boat for the islands.
A last breakfast in the garden, then a private water taxi from the hotel dock to Marco Polo airport. The trip ends on the lagoon.
The move: water taxi from your hotel’s dock to the airport.


Yes, at three nights each. That is the minimum I’d give each city, and with private transfers and the two train legs handled door to door, no day is lost to travel.
Fly into Rome and home from Venice. Rome is the easiest long-haul arrival, and leaving from Venice means the trip ends on the water instead of doubling back.
Between Rome, Florence and Venice, the fast train is quicker than the road, so I book it with porters and a meet-and-greet at both ends. If you’d rather not set foot in a station, a private car or helicopter works on every leg.
Yes. Either a day out with a driver from Florence, which is built into this route, or swap the three Florence nights for three in the countryside: Borgo San Felice near Siena, Il Borro for a honeymoon, or Castello di Casole for a traditional castle.
Spring and early autumn. Tell me your dates and I’ll tell you honestly how busy each city will be and which hotels still have the right rooms.
“Ten days in Italy, late May, our anniversary” is a complete answer. I’ll take it from there.